4-Chlorobenzaldehyde → 4-(Benzenesulfonyl)benzaldehyde

HRID 2076804Notes

Reaction equation

HRID 2076804 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[C:10]1([S:16]([O-:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[Na+]>CS(C)=O>[C:10]1([S:16]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 77264-ChlorobenzaldehydeHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 144174774-(Benzenesulfonyl)benzaldehydeYield 76.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
180 °C

Procedure

A microwave vessel was charged with 1 g of 4-chlorobenzaldehyde in 6 mL of DMSO and 1.75 g of sodium benzenesulfinate. The vessel was sealed and heated in a microwave reactor at 180° C. for 1.5 hours. The mixture was cooled and poured into 12 mL of ice water. Filtered and the solid was purified by flash chromatography using ethyl acetate/hexane as eluent mixtures to afford 1.34 g of the title compound. 76% yield.

Workup

  1. customThe vessel was sealed
  2. temperatureThe mixture was cooled
  3. filtrationFiltered
  4. customthe solid was purified by flash chromatography

Sources & evidence

ORD record
ord-d01eb62a3a674d85a96f5d8c6e30ec59
Source dataset
uspto-grants-2011_04
Patent number
US07928103B2

Reaction notes

Loading…